Since his early tales in which he'd pine over the popular and out-of-reach Liz Allan, Spider-Man has always been a desperate romantic. During the Stan Lee/Steve Ditko run, part of what made Peter Parker so relatable was that he wasn't a playboy Lothario—indeed, he'd suffer his fair share of unrequited crushes.

However, his fateful spider bite changed everything. Once Peter Parker reached college, he came out of his shell, managing to woo the likes of Gwen Stacy and Mary Jane Watson in the process. Over the years, Spider-Man has dated numerous beautiful, brilliant women who have complimented him exceptionally.

10 Bobbi Morse and Spider-Man Adventured Together

Spider-Man and Mockingbird began dating during the latter years of Dan Slott's run on The Amazing Spider-Man. Both were working for S.H.I.E.L.D. at the time, engaging in globe-trotting adventures together. Flirting on the job blossomed into a romance as the two heroes found synergy on and off the battlefield.

While Bobbi Morse was the right girlfriend for the right time, their love story did not last long. Mockingbird was an excellent support to Peter Parker—even allowing him to live with her when he fell on hard times—but they soon realized they had little in common besides their employer and correlative experience.

9 Jill Stacy Supported Spider-Man Through MJ's Presumed Death

Stacy women have a habit of capturing Spider-Man's heart, and Jill Stacy was no exception. Initially befriending Mary Jane Watson at Empire State University, Jill joined their friendship group and grew closer to Peter Parker, who was initially somewhat perturbed at how much she reminded him of the love of his life, Gwen Stacy.

When Mary Jane was presumed dead in a plane crash, the two grew even closer, this kinship eventually culminating in a romance. While it was short-lived, Jill was an amazing support to Peter through one of his most difficult times, and she had the decency to back away tactfully when Mary Jane inevitably returned.

8 Cindy Moon and Spider-Man Shared an Intense Chemistry

Cindy Moon, A.K.A. Silk, was bitten by the same spider that granted Spider-Man his powers. However, unlike Peter Parker, she spent most of her life in a specially designed bunker to protect her from the Inheritors. When she emerged and met Spider-Man, the two were immediately drawn to each other.

The pair found their shared spider powers made them biologically allured to each other on an intense level, leading to a whirlwind, passionate romance. However, due to the pheromonal nature of their attraction, Silk and Spidey shied away from each other romantically. Even so, they remained exceptional allies on the battlefield.

7 Ultimate Kitty Pryde and Spider-Man Made an Excellent Team on and off the Battlefield

Ultimate Spider-Man got together with Mary Jane Watson far sooner than his Earth-616 counterpart, but the two almost as swiftly broke up. Peter Parker dived into his Spider-Man persona to forget his woes, which led to numerous high-octane team-ups with the Ultimate X-Men, which is how he met Kitty Pryde.

The two immediately hit it off, with Kitty harboring a crush on Peter. Readers were treated to numerous charming dates between the two, and Kitty even adopted a new masked persona to allow them to fight crime together. Dating other superpowered individuals hasn't always worked out for Spider-Man, but Kitty remains one of the best.

6 Betty Brant was Spider-Man's First Love

Betty Brant holds a special place in Peter Parker's heart as his first true love. Initially J. Jonah Jameson's personal assistant at the Daily Bugle, the two dated for vast swathes of Stan Lee and Steve Ditko's run, with Betty helping Peter finally come out of his shell and get over Liz Allan.

However, the romance was not to last—Betty proved insecure at the time, and Peter's life as Spider-Man always got in the way. Though the two could not reconcile these differences, they remained steadfast and loyal friends, sharing many touching yet platonic moments together across Spider-Man's long publishing history.

5 Felicia Hardy Brought Excitement to Spider-Man's Life

The seductive and complicated Black Cat came crashing into Spider-Man's life as an antagonist who quickly developed into an ally. As the two grew closer, Felicia Hardy's attraction towards Spider-Man became evident, and the two began dating. Felicia brought much excitement to Spidey's life as the two fought against the New York mob.

However, the exhilaration soon fizzled out when it became apparent the Black Cat had no interest in the man behind the Wall-Crawler's mask. The two became great friends, with Spider-Man touchingly supporting Felicia through the harrowing events of The Evil That Men Do. The pair recently rekindled their romance, but Felicia called it off after a night out with the Beetle's crew.

4 Anna Maria Marconi Had a Brilliant Mind on Par With Peter Parker

A great leap forward for representation in comics, Anna Maria Marconi captured Otto Octavius's heart when he was body-swapped with Peter Parker during the events of The Superior Spider-Man. Strong, independent, and intellectually brilliant, Anna fiercely supported "Peter's" pursuits, and Otto even intended to propose to her.

Otto's love for Anna eventually led him to relinquish control of his stolen body back to Peter Parker to protect his great love from the madness of the Green Goblin. When the truth came out, Anna became an invaluable ally to Spider-Man, but Peter chose not to pursue the relationship further due to its unethical nature.

3 Carlie Cooper Helped Peter Parker Move On From Mary Jane

Initially portrayed as Lily Hollister's socially awkward friend, Carlie Cooper came into Spider-Man's life when Lily began dating Harry Osborn. While Carlie's insecurity meant she initially felt no one could see her when standing next to Lily, Peter Parker felt very differently, but it took a long time for the two to begin dating.

Once they did, however, the couple made an amazing team, with Carlie playing an intrinsic role in city-spanning events such as Spider-Island. As a quick-witted cop with a keen sense of justice, she complimented both Peter and Spider-Man. Most importantly, she made Peter believe in love again after his tragic split from Mary Jane during One More Day.

2 Gwen Stacy was Spider-Man's First Great Love

A fan favorite for good reason, Gwen Stacy stands as one of Spider-Man's greatest girlfriends. The two met when they were classmates at Empire State University, and Peter Parker couldn't believe his luck when he succeeded in turning the brilliant, smart, and beautiful Gwen's head. She always stuck up for Peter against the likes of Flash Thompson, and a slow-burning romance blossomed.

Tragically, Gwen is more defined by her premature death at the hands of the Green Goblin and the enduring hole that this left in Peter's heart. Fans looking to witness how much Gwen meant to Spidey should look no further than The Night Gwen Stacy Died and the pitch-perfect coda Spider-Man: Blue, with these stories exploring Gwen's enduring impact on Peter.

1 Mary Jane is Spider-Man's Ultimate Romance

"Face it, Tiger...you just hit the jackpot!" Mary Jane came crashing into Spider-Man's world with this singular iconic line, and nothing would be the same again. Though the likes of Gwen Stacy and Harry Osborn being on the scene meant it took a long time for this couple to get together, once they did, it led to one of Marvel's most celebrated and enduring romances.

Peter and Mary Jane underwent amazing character progression together as a couple, and the love and support they afforded one another across the decades was nothing short of touching. Tragically, Mephisto erased their marriage from existence during the infamous events of One More Day. However, fans can still turn to Renew Your Vows and Jonathan Hickman's superb Ultimate Spider-Man to witness a still happily married Peter and MJ at their best.